Disubstituted isothiazole azo dyes containing tetrahydroquinoline type couplers

Abstract

Disclosed are novel azo dyes containing an isothiazole diazo moiety which may be substituted, and a tetrahydroquinoline coupler which also may be substituted. The dyes produce red to violet shades on, for example, hydrophobic textile fiber including polyesters, polyamides, and cellulose esters and have excellent properties including lightfastness, washfastness and resistance to sublimation, and dye at unusually low energy levels. The dyes have the general formula ##STR1## wherein the various substituents, R 1 through R 9 , are selected from a wide variety of groups such as alkyl, --CN, halogen, alkoxy, and the like.

We claim: 
     
       1. A compound of the formula ##STR35## wherein R 1  and R 2  are each selected from cyano, bromo, chloro, formyl, lower alkoxycarbonyl, lower alkyl, lower alkylsulfonyl, thiocyanato, carbamoyl, lower alkylcarbamoyl, hydroxy substituted lower alkylcarbamoyl, and lower alkanoyl; R 3  and R 4  are each selected from hydrogen, fluorine, chlorine, bromine, lower alkyl, cycloalkyl, lower alkoxy, phenoxy, lower alkylthio, arylthio, and radicals having the formula --NH--X--R 10  in which X is --CO--, --COO--, or --SO 2  and R 10  is selected from lower alkyl and lower alkyl substituted with halogen, hydroxy, phenoxy, aryl, cyano, cycloalkyl, lower alkylsulfonyl, lower alkylthio, lower alkanoyloxy, or lower alkoxy, and when X is --CO--, R 10  also can be hydrogen, amino, lower alkylamino, lower dialkylamino, arylamino, aryl, or furyl;   R 5  is selected from hydrogen; cycloalkyl; cycloalkyl substituted with one or two groups selected from lower alkyl, --OH, lower alkoxy, halogen and hydroxy substituted lower alkyl; phenyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, lower alkanoylamino, cyano or lower alkoxycarbonyl; straight or branched lower alkenyl; straight or branched alkyl of 1-8 carbons; and straight or branched alkyl of 1-8 carbons substituted with the following: hydroxy; halogen; cyano; succinimido; glutarimido; phthalimido; 2-pyrrolidono; cyclohexyl; phenyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, lower alkanoylamino, cyano or lower alkoxycarbonyl; lower alkanoylamino; vinylsulfonyl; acrylamido; phthalimidinyl; benzoylsulfonicimidyl; lower alkylsulfonamido; phenylsulfonamido; lower alkoxycarbonylamino; lower alkylcarbamoyloxy; lower alkoxycarbonyl; lower alkoxycarbonyloxy; groups of the formula ##STR36##  wherein Y is --NH--, --NH--lower alkylene, --O--, --S--, or --CH 2  O--; --S--R 11  wherein R 11  is lower alkyl, phenyl, phenyl substituted with halogen, lower alkyl, lower alkoxy, lower alkanoylamino, cyano, or lower alkoxycarbonyl, pyridyl, pyrimidinyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, or ##STR37##  --OXR 10  ; --NH--X--R 10  ; --X--R 10  ; --CONR 12  R 12  ; --SO 2  NR 12  R 12  ; wherein R 10  and X are as defined as above and each R 12  is selected from H and R 10  ; lower alkoxy; lower alkoxy substituted with hydroxy, cyano, lower alkanoyloxy, or lower alkoxy; phenoxy; or phenoxy substituted with one or more of lower alkyl, lower alkoxy or halogen;   R 6 , R 7 , and R 8  are each selected from hydrogen and lower alkyl; and R 9  is selected from H, --OH, --Cl, --CONH 2 , --CONH--lower alkyl, lower alkoxy, phenoxy, --SR 11 , and --OXR 10  wherein R 10  and R 11  are as defined above.   
     
     
       2. A compound according to claim 1 having the formula ##STR38## 
     
     
       3. A compound according to claim 1 having the formula ##STR39## 
     
     
       4. A compound according to claim 1 having the formula ##STR40## 
     
     
       5. A compound according to claim 1 having the formula ##STR41##